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Eicosapentaenoyl ethanolamide

CAT: 0804-HY-124089-01Size: 5 mg (144.71 mM x 100 μL in Ethanol)Dry Ice: NoHazardous: No
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CAT#:0804-HY-124089-01Size:5 mg (144.71 mM x 100 μL in Ethanol)
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Eicosapentaenoyl ethanolamide, an omega-3 fatty acid, is one of N-acylethanolamines (NAEs) . Eicosapentaenoyl ethanolamide is cannabinoid CB1/CB2 receptor agonist. Eicosapentaenoyl ethanolamide acts as a metabolic signal. Eicosapentaenoyl ethanolamide inhibits dietary restriction (DR) -induced lifespan extension in wild type animals and suppresses lifespan extension in a TOR pathway mutant[1][2].
CAS Number
109001-03-8
UNSPSC
12352211
Hazard Statement
H225, H319
Target
Cannabinoid Receptor
Type
Reference compound
Related Pathways
GPCR/G Protein; Neuronal Signaling
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/eicosapentaenoyl-ethanolamide.html
Concentration
144.71 mM * 200 μL in Ethanol
Purity
98.38
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)NCCO
Molecular Formula
C22H35NO2
Molecular Weight
345.52
Precautions
H225, H319
References & Citations
[1]Mark Lucanic, et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature. 2011 May 12;473 (7346) :226-9.|[2]Iain Brown, et al. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis. 2010 Sep;31 (9) :1584-91.
Shipping Conditions
Blue Ice
Storage Conditions
Solution, -20°C, 2 years
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
CB1; CB2

Chemical Information

(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine

(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine is an N-acylethanolamine 20:5 that is the ethanolamide of (5Z,8Z,11Z,14Z17Z)-eicosapentaenoic acid. It has a role as a PPARgamma agonist. It is a N-acylethanolamine 20:5 and an endocannabinoid. It is functionally related to an all-cis-5,8,11,14,17-icosapentaenoic acid.

CAS Number109001-03-8
PubChem CID5283450
IUPAC Name(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
Molecular FormulaC22H35NO2
Molecular Weight345.5
XLogP4.7
Topological Polar Surface Area49.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count15
Heavy Atom Count25
Formal Charge0
Complexity445
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChI
InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey
OVKKNJPJQKTXIT-JLNKQSITSA-N
Chemical Structure
2D Structure
2D structure of (5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine
CAS: 109001-03-8
CID: 5283450
Formula: C22H35NO2
MW: 345.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight345.5
XLogP34.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count15
Exact Mass345.266779359
Monoisotopic Mass345.266779359
Topological Polar Surface Area49.3 Ų
Heavy Atom Count25
Formal Charge0
Complexity445
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count5
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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